[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]>C(Cl)Cl.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1To a 0° C. solution of 4-(4-bromophenyl)phenol (1.0 g, 4.0 mmol) and pyridine (0.65 mL, 8 mmol) in CH2Cl2 (20 mL) was added chloro-tert-butyldimethylsilane (0.72 g, 4.8 mmol). The resulting mixture was allowed to warm to room temperature and stirred for 3 days, then diluted with water and extracted with CH2Cl2. The organic layer was washed with a 2N HCl solution, a 1N KOH solution, dried (MgSO4) and concentrated under reduced pressure to yield 1-(4-bromophenyl)-4-tert-butyldimethylsilyloxybenzene (0.89 g, 61%) as a white solid: TLC (33% EtOAc/hex) Rf 0.57.
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